Both cognitive and sociocultural traditions have customarily theorised learning in terms of processes of progression within single communities. More recently, educational scholars have started to focus on learning as a horisontal process of boundary crossing between multiple communities. A problem of this approach is that boundaries are often laid out analytically on a system level, without explaining whether and how boundaries relate to discontinuities at the level of an individual student’s learning process. The latter requires theoretical elaboration on how an individual learner can, simultaneously, be part of more than one practice. By drawing on a dialogical approach to self, we intend to theorise learners as participants in practices, and as transcendent selves. In doing so, we point out that boundaries are dynamically evolving discontinuities that mediate or obstruct potential hybridisations of school and everyday life experiences in learning.